Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester
• CAS No.: 151805-85-5
• Molecular Formula: C₂₄H₃₄O₄SSi
• Molecular Weight: 446.683
• Mol file: 151805-85-5.mol

Synonyms:Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester

Chemical Property of Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester

There total 2 articles about Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methanesulfonyl chloride (124-63-0) + (3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-3-hexen-1-ol (150919-50-9) → Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester (151805-85-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1139/v93-153

Reference yield:

(3E/3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-1-tetrahydropyranyloxy-3-hexene → Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester (151805-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 355 mg / pyridinium p-toluenesulfonate (PPTS), i-PrOH / 4 h / 80 °C

2: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridinium p-toluenesulfonate; triethylamine; isopropyl alcohol; In dichloromethane;

DOI:10.1139/v93-153

Reference yield:

Methanesulfonic acid (Z)-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl ester (151805-85-5) → (5Z,11E,13Z)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6,14-dimethyl-pentadeca-5,11,13-trienoic acid methyl ester (151805-97-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH, 2.) KI / 1.) DMF, THF, 0 deg C, 1 h, 2.) DMF, THF, 70 deg C, 36 h

2: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

3: 83 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 15 h

5: 1.) NaH, 2.) KI / 1.) DMF, THF, 0 deg C, 1 h, 2.) DMF, THF, 85 deg C, 16 h

With tetrabutyl ammonium fluoride; sodium hydride; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1139/v93-153

upstream raw materials:

methanesulfonyl chloride

(3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-3-hexen-1-ol

Downstream raw materials:

2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester

(5Z,11E,13Z)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6,14-dimethyl-pentadeca-5,11,13-trienoic acid methyl ester

(5Z,11Z,13E)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6,14-dimethyl-pentadeca-5,11,13-trienoic acid methyl ester

(5Z,11E,13E)-15-(tert-Butyl-diphenyl-silanyloxy)-2,9,9-tris-methoxycarbonyl-6,14-dimethyl-pentadeca-5,11,13-trienoic acid methyl ester